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Deep generative models have recently been applied to molecule design. If the molecules are encoded in linear SMILES strings, modeling becomes convenient. However, models relying on string representations tend to generate invalid samples and…

Machine Learning · Computer Science 2020-10-20 Bo Pang , Tian Han , Ying Nian Wu

SMILES is a linear representation of chemical structures which encodes the connection table, and the stereochemistry of a molecule as a line of text with a grammar structure denoting atoms, bonds, rings and chains, and this information can…

Machine Learning · Computer Science 2018-12-03 Arindam Paul , Dipendra Jha , Reda Al-Bahrani , Wei-keng Liao , Alok Choudhary , Ankit Agrawal

In deep learning for drug discovery, chemical data are often represented as simplified molecular-input line-entry system (SMILES) sequences which allow for straightforward implementation of natural language processing methodologies, one…

Machine Learning · Computer Science 2023-10-05 Kathryn E. Kirchoff , Travis Maxfield , Alexander Tropsha , Shawn M. Gomez

Variational autoencoders (VAEs) defined over SMILES string and graph-based representations of molecules promise to improve the optimization of molecular properties, thereby revolutionizing the pharmaceuticals and materials industries.…

Machine Learning · Computer Science 2019-06-04 Zaccary Alperstein , Artem Cherkasov , Jason Tyler Rolfe

In drug-discovery-related tasks such as virtual screening, machine learning is emerging as a promising way to predict molecular properties. Conventionally, molecular fingerprints (numerical representations of molecules) are calculated…

Machine Learning · Computer Science 2019-11-13 Shion Honda , Shoi Shi , Hiroki R. Ueda

In the computational prediction of chemical compound properties, molecular descriptors and fingerprints encoded to low dimensional vectors are used. The selection of proper molecular descriptors and fingerprints is both important and…

Machine Learning · Computer Science 2020-10-23 Sangrak Lim , Yong Oh Lee

Deep generative models are increasingly becoming integral parts of the in silico molecule design pipeline and have dual goals of learning the chemical and structural features that render candidate molecules viable while also being flexible…

Biomolecules · Quantitative Biology 2021-06-08 Yair Schiff , Vijil Chenthamarakshan , Karthikeyan Natesan Ramamurthy , Payel Das

Optimizing molecular design and discovering novel chemical structures to meet certain objectives, such as quantitative estimates of the drug-likeness score (QEDs), is NP-hard due to the vast combinatorial design space of discrete molecular…

Machine Learning · Computer Science 2023-02-23 Mohammad Sajjad Ghaemi , Hang Hu , Anguang Hu , Hsu Kiang Ooi

A major challenge in computational chemistry is the generation of novel molecular structures with desirable pharmacological and physiochemical properties. In this work, we investigate the potential use of autoencoder, a deep learning…

Machine Learning · Computer Science 2017-11-22 Thomas Blaschke , Marcus Olivecrona , Ola Engkvist , Jürgen Bajorath , Hongming Chen

AI for drug discovery has been a research hotspot in recent years, and SMILES-based language models has been increasingly applied in drug molecular design. However, no work has explored whether and how language models understand the…

Machine Learning · Computer Science 2024-01-17 Xiuyuan Hu , Guoqing Liu , Yang Zhao , Hao Zhang

Chemical language models (CLMs) are prominent for their effectiveness in exploring chemical space and enabling molecular engineering. However, while exploring chemical-linguistic space, CLMs suffer from the gap between natural language and…

Computational Engineering, Finance, and Science · Computer Science 2025-01-07 Liuzhenghao Lv , Hao Li , Yu Wang , Zhiyuan Yan , Zijun Chen , Zongying Lin , Li Yuan , Yonghong Tian

This study introduces a novel approach, combining substruct counting, $k$-mers, and Daylight-like fingerprints, to expand the representation of chemical structures in SMILES strings. The integrated method generates comprehensive molecular…

Biomolecules · Quantitative Biology 2024-04-01 Sarwan Ali , Prakash Chourasia , Murray Patterson

Descriptor generation methods using latent representations of encoder$-$decoder (ED) models with SMILES as input are useful because of the continuity of descriptor and restorability to the structure. However, it is not clear how the…

Chemical Physics · Physics 2023-04-14 Shumpei Nemoto , Tadahaya Mizuno , Hiroyuki Kusuhara

Models based on machine learning can enable accurate and fast molecular property predictions, which is of interest in drug discovery and material design. Various supervised machine learning models have demonstrated promising performance,…

Machine Learning · Computer Science 2022-12-15 Jerret Ross , Brian Belgodere , Vijil Chenthamarakshan , Inkit Padhi , Youssef Mroueh , Payel Das

Molecule generation is a task made very difficult by the complex ways in which we represent molecules computationally. A common technique used in molecular generative modeling is to use SMILES strings with recurrent neural networks built…

Biomolecules · Quantitative Biology 2024-02-28 Divahar Sivanesan

Chemical representation learning has gained increasing interest due to the limited availability of supervised data in fields such as drug and materials design. This interest particularly extends to chemical language representation learning,…

Chemical Physics · Physics 2024-08-06 Jun-Hyung Park , Yeachan Kim , Mingyu Lee , Hyuntae Park , SangKeun Lee

We propose a novel molecular fingerprint-based variational autoencoder applied for molecular generation on real-world drug molecules. We define more suitable and pharma-relevant baseline metrics and tests, focusing on the generation of…

Machine Learning · Computer Science 2022-11-17 Ruslan N. Tazhigulov , Joshua Schiller , Jacob Oppenheim , Max Winston

Recent advancements in computational chemistry have leveraged the power of trans-former-based language models, such as MoLFormer, pre-trained using a vast amount of simplified molecular-input line-entry system (SMILES) sequences, to…

Biomolecules · Quantitative Biology 2024-11-05 Tianhao Peng , Yuchen Li , Xuhong Li , Jiang Bian , Zeke Xie , Ning Sui , Shahid Mumtaz , Yanwu Xu , Linghe Kong , Haoyi Xiong

Chemical databases store information in text representations, and the SMILES format is a universal standard used in many cheminformatics software. Encoded in each SMILES string is structural information that can be used to predict complex…

Machine Learning · Statistics 2018-08-16 Garrett B. Goh , Nathan O. Hodas , Charles Siegel , Abhinav Vishnu

Since the advent of machine learning, interpretability has remained a persistent challenge, becoming increasingly urgent as generative models support high-stakes applications in drug and material discovery. Recent advances in large language…

Machine Learning · Computer Science 2025-12-10 Jaron Cohen , Alexander G. Hasson , Sara Tanovic
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